Cool and Underrated Towns in the Midwest

Cool and Underrated Towns in the Midwest

BY Matt Meltzer | December 6, 2023

“The Midwest” carries with it a variety of connotations. Friendly people. Sprawling lakes. Cheese. But also a hard-working, salt-of-the-earth ethos: people here mean what they say. If you’re from a different part of the country, visiting the Midwest is a trip into honest country. You’ll be constantly surprised by the genuineness of the people and the landscape. 

Its big cities like Kansas City, Detroit and Milwaukee are always a good time. However, to really discover what the Midwest is about, you need to delve into its smaller towns, where everyone greets you with a hello and knows your name by the end of the weekend. From the Great Lakes to the Great Prairies, here’s 10 of the coolest and most underrated towns in the middle of the country.

Abilene, Kansas, USA - July 9, 2019: The house where President Eisenhower used to live when it was a little boy is now an attraction. Photo via Shutterstock.
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Abilene, Kansas, USA - July 9, 2019: The house where President Eisenhower used to live when it was a little boy is now an attraction. Photo via Shutterstock.

Abilene, Kan.

Abilene, Kan, USA

The lure of the Dwight D. Eisenhower Presidential Library is a strong one, we know, but even those not completing their presidential library bingo card will enjoy Abilene. It’s got one of the most impressive collections of old Victorian houses anywhere in the Midwest, and, if you visit during Christmas, you’ll find them decked out in over-the-top lights and graceful poinsettias. Small-town Kansas is also an unlikely place for a James Beard Award-winning restaurant, but stop in for a fried chicken dinner at the Brookville Hotel and you’ll see why it’s so celebrated.

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Beloit Iron Works mural at the edge of the Rock River. Photo via Shutterstock.
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Beloit Iron Works mural at the edge of the Rock River. Photo via Shutterstock.

Beloit, Wis.

Beloit, Wis, USA

Quick quiz: What is the smallest city in America with professional sports? If you’re good with context clues, you probably guessed Beloit, Wis., home of the Miami Marlins’ A-ball affiliate Sky Carp. Their stadium is one of the true Minor League treasures with its panoramic view of Beloit’s classic redbrick downtown. On Saturdays, you can stroll a farmers market that draws vendors from across the state, then kick back for a rooftop beer at the Hotel Goodwin. Hidden in all that redbrick you’ll find hints of hip that have trickled down from Madison, like the taco-and-vintage-furniture dive 5Bar, or the creative salads and organic food at Bushel & Peck’s. Beloit is a perfect weekend getaway to a slower, simpler pace, with just enough cool to keep anyone entertained.

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10-19-2019 Bloomington USA - University of Indiana - Family walks with college student out main gates of campus down into the town during Fall Break weekend. Photo via Shutterstock.
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10-19-2019 Bloomington USA - University of Indiana - Family walks with college student out main gates of campus down into the town during Fall Break weekend. Photo via Shutterstock.

Bloomington, Ind.

Bloomington, Ind, USA

Arguments abound over which Big 10 school has the best college town. But how many of them can claim John Mellencamp as a native son? Celebrity singers aside, Bloomington also has the best food scene in the B1G. A trip down Fourth Street is a world tour of Tibetan, Burmese, Korean and Cajun restaurants beckoning hungry Hoosiers. The city is also home to five breweries, enough for a full day of beer hopping between Metal Works, The Tap and Upland. Then there is the basketball team, which, while not what it was under the late Bobby Knight, still brings one of the best atmospheres in the country.

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Elms Hotel and Spa
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Elms Hotel and Spa

Excelsior Springs, Mo.

Excelsior Springs, MO, USA

Excelsior Springs is probably best known as home to the luxe Elms Hotel and Spa, a grand Gilded Age hotel that housed Harry Truman the night the world thought he’d lost an election. The legendary haunted hotel is reason enough to travel to northeast Missouri, but the town it calls home is packed with other cool attractions. A trolley tour takes you through the area’s breweries and wineries, most notably Dubious Claims Brewing and Four Horses and a Dog Winery. The historic downtown has a clever collection of boutiques and art galleries, all but ensuring you go home with at least one thing you never planned on buying. You can also immerse yourself in Midwestern culture at Ray’s Diner, a classic Missouri greasy spoon that’s been going strong since 1947.

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Galena, IL, United States - October 9, 2022: View of Main Street in historical downtown area of Galena, Illinois. Photo via Shutterstock.
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Galena, IL, United States - October 9, 2022: View of Main Street in historical downtown area of Galena, Illinois. Photo via Shutterstock.

Galena, Ill.

Galena, IL, USA

Galena is the small Midwestern town by which all others are judged, the picture of historic preservation and local charm. The Greek and Italianate buildings that line downtown look like a postcard from the 1900s, and inside you’ll find boutiques, coffee shops and bustling local bars. Old and charming can quickly turn creaky and spooky come nightfall. Local-led ghost tours tell stories of the spirits that are as well preserved as the buildings. Galena was also home of former president Ulysses S. Grant, and you can visit his home during daily tours.

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Split Rock Lighthouse on Lake Superior
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Split Rock Lighthouse on Lake Superior. Photo via Shutterstock.

Grand Marais, Minn.

Grand Marais, Minn, USA

It might be tempting to speed through Grand Marias as you make your way from Duluth to the Canadian border along the stunning North Shore Scenic Drive, but do your best to resist. In fact, Grand Marias is probably the best place to book a room if you’re exploring the road, sitting just a short drive from the waterfalls of Gooseberry Falls State Park and the iconic Split Rock Lighthouse. Minnesota’s only black sand beach isn’t far either, a little slice of cold-weather Maui along the Great Lakes. In town, you’d be remiss not to grab a pizza at Sven and Ole’s, where Nordic locals are the picture of Midwestern nice. You can also hit  Voyageur Brewing’s taproom, one of the region’s most popular breweries.

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Hotel Grinnell in Grinnell, Iowa.
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Hotel Grinnell in Grinnell, Iowa.

Grinnell, Iowa

Grinnell, Iowa, USA

The coolest small town in Iowa didn’t just bring us its namesake run-and-gun style of basketball. This college town between Des Moines and Iowa City is also an architectural standout, anchored by the visitors center inside the Louis Sullivan Bank. Grinnell also turned its old junior high into the Hotel Grinnell, where every room includes a chalkboard and the restaurant, Periodic Table, is pun-tastic. You’ll also find wine bars and independent restaurants lining its charming downtown, making Grinnell the kind of place you’ve never heard of, then don’t stop talking about.

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Aerial View of the Tourist Town of Medora, North Dakota outside of Theodore Roosevelt National Park. Photo via Shutterstock.
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Aerial View of the Tourist Town of Medora, North Dakota outside of Theodore Roosevelt National Park. Photo via Shutterstock.

Medora, N.D.

Medora, N.D., USA

Just outside Theodore Roosevelt National Park sits this city of 117 people nestled in the North Dakota Badlands. The former cattle town has been restored to a full-fledged Old West resort, where you can meander down wooden sidewalks past swinging-door saloons. The difference is in Medora, said saloons are slinging Certified Angus Beef steaks, and the lodging, from the restored Badlands Motel to the luxe Rough Riders Hotel, is also upscale. Medora’s big draw is the Medora Musical, an all-American revue set in one of the coolest venues in the country with views over the Badlands. Before the show, indulge in steak fondue, a traditional dinner where NY strips are cooked in barrels of hot oil and served with a full picnic buffet.

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Bear Country U.S.A. is 250-acre drive-through bear park w/wolves, big horn sheep, elk, plenty of black bear, grizzly bear, lynx, bobcat, coyote, beaver, badger. Photo via Shutterstock.
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Rapid City, S.D., U.S.A. Sept. 15, 2018. Bear Country U.S.A. is 250-acre drive-through bear park w/wolves, big horn sheep, elk, plenty of black bear, grizzly bear, lynx, bobcat, coyote, beaver, badger. Photo via Shutterstock.

Rapid City, S.D.

Rapid City, SD, USA

Far more than the gateway to Mt. Rushmore, this city nestled in the Black Hills is an artsy, creative oasis in the vast grasslands of South Dakota. It’s a short drive to the stunning scenery of Spearfish Canyon and the abundant wildlife in Custer State Park. It’s also got an alluring, walkable downtown.You can sample craft beers in an old firehouse at Firehouse Brewing, or play vintage arcade games while you drink at Press Start. Rapid City is also home to a large Nepalese population, and you can go on a venerable Himalayan food crawl between Kathmandu Bistro, Everest Cuisine and Himalayan Kitchen. You can even ski in Rapid City if you know where to look: you’ll find a pretty decent day hill at Terry Peak about 45 minutes away.

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Wamego, Kansas, United States - June 13 2023: a green museum building on the main street. Photo via Shutterstock.
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Wamego, Kansas, United States - June 13 2023: a green museum building on the main street. Photo via Shutterstock.

Wamego, Kan.

Wamego, Kan, USA

Do you love “The Wizard of Oz”? Like, did you dress up in ruby slippers as a kid and refuse to wear anything else? Then a trip to Wamego, Kan., is probably in order. Though it’s not officially the spot where Dorothy’s house was uprooted, it’s pretty darn close. And it’s home to the Oz Museum, a bright green downtown building containing the largest private collection of “Wizard of Oz” artifacts in the world. Oz lovers have more than a museum to explore, though: the city also has a real Yellow Brick Road, the Oz Winery and an annual gathering of movie lovers called OzFest (unrelated to the Prince of Darkness). Interestingly, it’s also the birthplace of Walter P. Chrysler, and his boyhood home could easily stand in for Dorothy’s.

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